This series is comprised primarily of journals and correspondence of Irene Sherman Gillespie and her daughter, Phyllis Gillespie Schumacher. Financial and legal documents from the 1930s and 1960s are also included; some of these document difficulties paying debts in the early 1930s, perhaps connected to the economic downturn after the stock market crash of 1929. Other materials include a 1908 roster of the Society of the Cincinnati as well as documents pertaining to Lawrence L. Gillespie. A manuscript written by Major General George L. Gillespie is included in this series as well.